Improving oral bioavailability of peptides by multiple N-methylation: Somatostatin analogues

Eric Biron, Jayanta Chatterjee, Oded Ovadia, Daniel Langenegger, Joseph Brueggen, Daniel Hoyer, Herbert A. Schmid, Raz Jelinek, Chaim Gilon, Amnon Hoffman, Horst Kessler

Research output: Contribution to journalArticlepeer-review

257 Scopus citations

Abstract

Full methyl jacket? A complete library of the N-methylated somatostatin cyclopeptidic analogue Veber-Hirschmann peptide cyclo(-PFwKTF-) has been prepared with the aim of improving its bioavailability. Several analogues from the library were found to bind to the somatostatin receptor in the nanomolar range and one of them shows a significant oral bioavailability of 10%. Conformational analysis shows that N-methylationis allowed at specific positions without affecting the bioactive conformation. (Figure Presented)

Original languageEnglish
Pages (from-to)2595-2599
Number of pages5
JournalAngewandte Chemie - International Edition
Volume47
Issue number14
DOIs
StatePublished - 25 Mar 2008

Keywords

  • Bioavailability
  • Cyclic peptides
  • N methylation
  • Peptide drugs
  • Somatostatin

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)

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